4′-(4-Fluorophenyl)-1′-methyldispiro[indane-2,2′-pyrrolidine-3′,2′′-indane]-1,3,1′′-trione methanol hemisolvate

Mohamed Ashraf Ali,Elumalai Manogaran,Tan Soo Choon,Ibrahim Abdul Razak,Mohd Mustaqim Rosli

doi:10.1107/s1600536813009987

Mohamed Ashraf Ali, Elumalai Manogaran + Show 3 more

Open Access

https://doi.org/10.1107/s1600536813009987

Copy DOI

Abstract

The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent molecules and a one methanol solvent molecule. The methanol molecule is O—H⋯O hydrogen bonded to one of the independent molecules. The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent molecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one molecule, and 72.78 (8) and 77.27 (8)° in the other. In each molecule, a weak intramolecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds link the molecules into a three-dimensional network.

Highlights

The asymmetric unit of the title compound, C29H24FNO50.5CH3OH, contains two independent molecules and a one methanol solvent molecule
The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro
B adopt a half-chair conformation with the puckering parameters Q = 0.4612 (16) Å, φ = 127.36 (19)° for molecule A

Summary

Structure Reports

40 -(4-Fluorophenyl)-10 -methyldispiro[indane-2,20 -pyrrolidine-30 ,20 0 -indane]1,3,10 0 -trione methanol hemisolvate. H O hydrogen bonded to one of the independent molecules. The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7) in one independent molecule and 31.16 (8) in the other. The fluorosubstituted benzene ring forms dihedral angles of 65.35 (6). 85.87 (7) with the indane group benzene rings in one molecule, and 72.78 (8) and 77.27 (8) in the other. A weak intramolecular C—H O hydrogen bond forms an S(6) ring motif. Weak C—H O, C—H N and C—H F hydrogen bonds link the molecules into a three-dimensional network

Related literature

Bruker APEX DUO CCD areadetector diffractometer

Abdul Razak

Special details